City of London
Trail Running Calendar near City of London 2026-2027
Explore the top trail runs near City of London for 2026-2027! We've gathered 222 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
May 2027
A 10th anniversary half marathon and new 10k in Chislehurst that explores local green spaces and raises funds for The Maypole Project.
Trail races of 10 mile and 5 mile at Cammas Hall Farm, Essex on 16 May 2027 with chip timing, water stations and finisher t-shirt and medal.
A 50 km multi terrain ultra in Maidenhead along the Thames Path, Jubilee River and Green Way with chip timing, four aid stations, live tracking and a cut off of 8 hours 57 minutes.
Track event on a 400 metre athletics track offering distances from 5k to 50k plus a six hour challenge at Wodson Park, limited to 100 entrants.
A guided trail half marathon around the Surrey Hills, about 13 miles from St Martha's Hill in Guildford, following parts of the North Downs Way and notable viewpoints. The run is social in format with a guided pace and evening options.
A supported trail event from Richmond to Brighton offering 100 km, 50 km, 25 km and marathon options with rest stops, GPS tracking, medical support and camping.
June 2027
A 5k obstacle course at Royal Windsor Racecourse with mud obstacles to climb, crawl and slide, mixed tarmac and grass surfaces, staggered wave starts and a minimum age of 13. Earlybird entry prices and a fundraising target apply.
A point-to-point 50 km trail along the River Medway from Rochester to Tonbridge with four aid stations, live timing and an athletics track finish.
Two supported trail options in London - a 55 km ultra and a 25 km trail run along the Capital Ring, finishing at Richmond Green with feed stations and chip timing.
A 10 km out-and-back race through gravel paths and woodland at Weald Country Park in Brentwood, organised by MCC Promotions. The event includes on-day registration, water stations, prizes and supports the charity Sport In Mind.
Urban 100 km ultramarathon in central London with 100 km, 50 km and 25 km routes that pass 100+ city landmarks and include staffed checkpoints.
A muddy 5k obstacle course at Cassiobury Park where participants climb, crawl and slide through timed waves while raising funds for cancer research.
A 75 mile off road ultra on a one mile loop at Denbies Wine Estate with up to 30 hours to finish, chip timing and multiple concurrent race options.
A 100 mile ultra on a flat one mile trail loop at Denbies Wine Estate offering 12 hour and 24 hour options plus 50, 75 and shorter races.
A 24 hour attended challenge at Denbies Wine Estate in Dorking where runners complete 1 mile on the hour for 24 consecutive hours; onsite tent camping, daytime cafe service and a simultaneous virtual option are provided.